Arachidonic Acid
Daniele Piomelli
Professor of Pharmacology
360 Med Surge II
University of California, Irvine
Irvine, CA 92697-4625
Tel: (949) 824-6180
Fax: (949) 824-6305
E-Mail: piomelli@uci.edu
REFERENCES
1. Allen AC, Gammon CM, Ousley AH, McCarthy KD, Morell P. Bradykinin stimulates arachidonic acid release through the sequential actions of an sn-1 diacylglycerol lipase and a monoacylglycerol lipase. J Neurochem 1992;58:11301139.
2. Amruthesh SC, Falck JR, Ellis EF. Brain synthesis and cerebrovascular action of epoxygenase metabolites of arachidonic acid. J Neurochem 1992;58:503510.
3. Barbour B, Szatkowski M, Ingledew N, Attwell D. Arachidonic acid induces a prolonged inhibition of glutamate uptake into glial cells. Nature 1989;342:918920.
4. Belardetti F, Campbell WB, Falck JR, Demontis G, Rosolowsky M. Products of heme-catalyzed transformation of the arachidonate derivative 12-HPETE open S-type K+ channels in Aplysia. Neuron 1989;3:497505.
5. Bell RL, Kennerly DA, Stanford N, Majerus PW. DG lipase: a pathway for arachidonate release from human platelets. Proc Natl Acad Sci USA 1979;76:32383241.
6. Bliss TVP, Collingridge GL. A synaptic model of memory: long-term potentiation in the hippocampus. Nature 1993;361:3139.
7. Burch RM. G protein regulation of phospholipase A2. Mol Neurobiol 1989;3:155171.
8. Clark JD, Lin L-L, Kriz RW, Ramesha CS, Sultzman LA, Lin AY, Milona N, Knopf JL. A novel arachidonic acid-selective cytosolic PLA2 contains a Ca2+-dependent translocation domain with homology to PKC and GAP. Cell 1991;65:10431051.
9. Coleman RA. Methods in prostanoid receptors classification. In: Benedetto C, McDonald-Gibson RG, Nigam S, Slater T, eds. Prostaglandins and related substances. A practical approach. Oxford: IRL Press, 1987;267303.
10. De George JJ, Noronha JG, Bell J, Rapoport SI. Intravenous injection of (14C) arachidonate to examine regional brain lipid metabolism in unanesthetized rat. J Neurosci Res 1989;24:413423.
11. Deka N, Sun GY, MacQuarrie R. Purification and properties of acyl-CoA:1-acyl-sn-glycero-3-phosphocholine-O-acyltransferase from bovine brain microsomes. Arch Biochem Biophys 1986; 246:554563.
12. Dennis EA. Phospholipases. In: Abelson JN, Simon MI, eds. Methods in enzymology. San Diego: Academic Press, 1991.
13. Devane WA, Hanus L, Breuer A, Pertwee RG, Stevenson LA, Griffin G, Gibson D, Mandelbaum A, Etinger A, Mechoulam R. Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science 1992;258:19461949.
14. Dumuis A, Sebben M, Haynes L, Pin JP, Bockaert J. NMDA receptors activate the arachidonic acid cascade system in striatal neurons. Nature 1988;336:6870.
15. Exton JH. Signaling through phosphatidylcholine breakdown. J Biol Chem 1990;265:14.
16. Farooqui AA, Taylor WA, Horrocks LA. Characterization and solubilization of membrane bound diacylglycerol lipases from bovine brain. Int J Biochem 1986;18:991997.
17. Felder CC, Kanterman RY, Ma AL, Axelrod J. Serotonin stimulates phospholipase A2 and the release of arachidonic acid in hippocampal neurons by a type 2 serotonin receptor that is independent of inositolphospholipid hydrolysis. Proc Natl Acad Sci USA 1990;87:21872191.
18. Felder CC, Williams HL, Axelrod J. A transduction pathway associated with receptors coupled to the inhibitory guanine nucleotide binding protein Gi that amplifies ATP-mediated arachidonic acid release. Proc Natl Acad Sci USA 1991;88:64776480.
19. Freeman EJ, Damron DS, Terrian DM, Dorman RV. 12-Lipoxygenase products attenuate the glutamate release and Ca2+ accumulation evoked by depolarization of hippocampal mossy fiber nerve endings. J Neurochem 1991;56:10791082.
20. Gustafsson LE. Mechanisms involved in the action of prostaglandins as modulators of neurotransmission. In: Barkai AI, Bazan NG, eds. Arachidonic acid metabolism in the nervous system. Annals of the New York Academy of Sciences, vol 559. New York: New York Academy of Sciences, 1989;178191.
21. Harish OE, Poo M-M. Retrograde modulation at developing neuromuscular synapses: involvement of G protein and arachidonic acid cascade. Neuron 1992;9:12011209.
22. Hayaishi H, Fuji Y, Watanabe K, Hayaishi O. Enzymatic formation of prostaglandin F2a in human brain. Neurochem Res 1990;15:385392.
23. Hedqvist P, Brundin J. Inhibition by prostaglandin E1 of noradrenaline release and of effector response to nerve stimulation in the cat spleen. Life Sci 1969;8:389395.
24. Hedqvist P. Basic mechanisms of prostaglandin action on autonomic neurotransmission. Annu Rev Pharmacol Toxicol 1977;17:259279.
25. Herrero I, Miras-Portugal MT, Sanchez-Prieto J. Positive feedback of glutamate exocytosis by metabotropic presynaptic receptor stimulation. Nature 1992;360:163165.
26. Horrocks LA. Sources for brain arachidonic acid uptake and turnover in glycerophospholipids. In: Barkai AI, Bazan NG, eds. Arachidonic acid metabolism in the nervous system. Annals of the New York Academy of Sciences, vol 559. New York: New York Academy of Sciences, 1989;1724.
27. Jelsema CL. Light activation of phospholipase A2 in rod outer segments of bovine retina and its modulation by GTP-binding proteins. J Biol Chem 1987;262:163168.
28. Jelsema CL, Axelrod J. Stimulation of phospholipase A2 activity in bovine rod outer segment by the bg subunits of transducin and its inhibition by the a subunit. Proc Natl Acad Sci USA 1987;84:36253627.
29. Junier MP, Dray F, Blair I, Capdevila J, Dishman E, Falck JR, Ojeda S. Epoxygenase products of arachidonic acid are endogenous constituents of the hypothalamus involved in D2 receptor-mediated, dopamine-induced release of somatostatin. Endocrinology 1990; 126:15341540.
30. Kanterman RY, Felder CC, Brenneman DE, Ma AL, Fitzgerald S, Axelrod J. a1-Adrenergic receptor mediates arachidonic acid release in spinal cord neurons independent of inositol phospholipid turnover. J Neurochem 1990;54:12251232.
31. Keller M, Jackisch R, Seregi A, Hertting G. Comparison of prostanoid forming capacity of neuronal and astroglial cells in primary culture. Neurochem Int 1985;7:655665.
32. Kiesel L, Przylipiak AF, Habenicht AJR, Przylipiak MS, Runnebaum B. Production of leukotrienes in gonadotropin-releasing hormone-stimulated pituitary cells: potential role in luteinizing hormone release. Proc Natl Acad Sci USA 1991;88:88018805.
33. Kurachi Y, Ito H, Sugimoto T, Shimizu T, Miki I, Ui M. Arachidonic acid metabolites as intracellular modulators of the G protein-gated cardiac K+ channel. Nature 1989;337:555557.
34. Kurachi Y, Ito H, Sugimoto T, Shimizu T, Miki I, Ui M. a-Adrenergic activation of the muscarinic K+ channel is mediated by arachidonic acid metabolites. Pflugers Arch 1989;414:102104.
35. Laposata M, Reich EL, Majerus PW. Arachidonoyl-CoA synthetase. Separation from non-specific acyl-CoA synthetase and distribution in various cells and tissues. J Biol Chem 1985;260:1101611020.
36. Lazarewicz JW, Wroblewki JT, Palmer ME, Costa E. Activation of N-methyl-D-aspartate-sensitive glutamate receptors stimulates arachidonic acid release in primary cultures of cerebellar granule cells. Neuropharmacology 1988;27:765769.
37. Linden DJ, Sheu F-S, Murakami K, Routtemberg A. Enhancement of long-term potentiation by cis-unsaturated fatty acid: relation to protein kinase C and phospholipase A2. J Neurosci 1987;7:37833792.
38. Linden DJ, Smeyne M, Sun SC, Connor JA. An electrophysiological correlate of protein kinase C isozyme distribution in cultured cerebellar neurons. J Neurosci 1992;12:36013608.
39. Lindgren JA, Hökfelt T, Dahlén SE, Patrono C, Samuelsson B. Leukotrienes in the rat central nervous system. Proc Natl Acad Sci USA 1984;81:62126216.
40. Malmberg AB, Yaksh TL. Hyperalgesia mediated by spinal glutamate or substance P receptor blocked by spinal cyclooxygenase inhibition. Science 1992;257:12761279.
41. McGiff JC. Cytochrome P450 metabolism of arachidonic acid. Annu Rev Pharmacol Toxicol 1991;31:339369.
42. Miller B, Sarantis M, Traynelis SF, Attwell D. Potentiation of NMDA receptor currents by arachidonic acid. Nature 1992; 355:722725.
43. Montarolo PG, Kandel ER, Schacher S. Long-term heterosynaptic inhibition in Aplysia. Nature 1988;333:171174.
44. Montarolo PG, Glanzman DL, Kandel ER, Schacher S. cAMP and arachidonic acid induce opposite morphological changes with long-term presynaptic facilitation and inhibition in the sensory neurons of Aplysia. Soc Neurosci Abstr 1991;17:1591.
45. Moore SA, Yoder E, Spector AA. Role of the bloodbrain barrier in the formation of long-chain w-3 and w-6 fatty acids from essential fatty acid precursors. J Neurochem 1990;55:391402.
46. Moore SA, Yoder E, Murphy S, Dutton GR, Spector AA. Astrocytes, not neurons, produce docosahexaenoic acid (22:6 w-3) and arachidonic acid (20:4 w-6). J Neurochem 1991;56:518524.
47. Naor Z, Shearman MS, Kishimoto A, Nishizuka Y. Calcium-independent activation of hypothalamic type I protein kinase C by unsaturated fatty acids. Mol Endocrinol 1988;2:10431048.
48. Neufeld EJ, Sprecher H, Evans RW, Majerus P. A mutant HSDM1C1 fibrosarcoma line selected for defective eicosanoid precursor uptake lacks arachidonate-specific acyl-CoA synthetase. J Biol Chem 1984;259:19861992.
49. Nicol GD, Klingberg DK, Vasko MR. Prostaglandin E2 increases calcium conductance and stimulates release of substance P in avian sensory neurons. J Neurosci 1992;12:19171927.
50. Nishiyama M, Okamoto H, Watanabe T, Hori T, Hada T, Ueda N, Yamamoto S, Tsukamoto H, Watanabe K, Kirino T. Localization of arachidonate 12-lipoxygenase in canine brain tissues. J Neurochem 1992;58:13951400.
51. Nishiyama M, Watanabe T, Ueda N, Tsukamoto H, Watanabe K. Arachidonate 12-lipoxygenase is localized in neurons, glial cells and endothelial cells of the canine brain. J Histochem Cytochem 1993;41:111117.
52. Ogorochi T, Ujiara M, Narumiya S. Purification and properties of prostaglandin H-E isomerase from the cytosol of human brain: identification as anionic forms of glutathione transferase. J Neurochem 1987;48:900909.
53. Ordway RW, Singer JJ, Walsh JV. Direct regulation of ion channels by fatty acids. Trends Neurosci 1991;14:96100.
54. Pace-Asciak CR, Granström E, Samuelsson B. Arachidonic acid epoxides. Isolation and structure of two hydroxy epoxide intermediates in the formation of 8,11,12- and 10,11,12-trihydroxyeicosatrienoic acids. J Biol Chem 1983;258:68356840.
55. Pace-Asciak CR. Formation and metabolism of hepoxilin A3 by the rat brain. Biochem Biophys Res Commun 1988;151:493498.
56. Palmer MR, Palmer MR, Hoffer BJ, Murphy RC. Electrophysiological response of cerebellar Purkinje neurons to leukotriene D4 and B4. J Pharmacol Exp Ther 1981;219:9196.
57. Partington CR, Edwards MW, Daly JW. Regulation of cAMP formation in brain tissue by a-adrenergic receptors: requisite intermediacy by prostaglandins of the E-series. Proc Natl Acad Sci USA 1980;77:30243028.
58. Piomelli D, Shapiro E, Feinmark SJ, Schwartz JH. Metabolites of arachidonic acid in the nervous system of Aplysia: possible mediators of synaptic modulation. J Neurosci 1987;7:36753686.
59. Piomelli D, Volterra A, Dale N, Siegelbaum SA, Schwartz JH, Belardetti F. Lipoxygenase metabolites of arachidonic acid as second messengers for presynaptic inhibition in Aplysia sensory cells. Nature 1987;328:3843.
60. Piomelli D, Feinmark SJ, Shapiro E, Schwartz JH. Formation and biological activity of 12-keto-eicosatetraenoic acid in the nervous system of Aplysia. J Biol Chem 1988;263:1659116596.
61. Piomelli D, Shapiro E, Zipkin R, Schwartz JH, Feinmark SJ. Formation and action of 8-hydroxy-11,12-epoxy-5,9,14-icosatrienoic acid in Aplysia: a possible second messenger in neurons. Proc Natl Acad Sci USA 1989;86:17211725.
62. Piomelli D, Wang JKT, Sihra TS, Nairn AC, Czernik AJ, Greengard P. Inhibition of Ca2+/calmodulin-dependent protein kinase II by arachidonic acid metabolites. Proc Natl Acad Sci USA 1989; 86:85508554.
63. Piomelli D, Pilon C, Giros B, Sokoloff P, Martres MP, Schwartz JC. Dopamine activation of the arachidonic acid cascade as a basis for D1/D2 receptor synergism. Nature 1991;353:164167.
64. Ponzoni M, Montaldo PG, Cornaglia-Ferraris P. Stimulation of receptor-coupled phospholipase A2 by interferon-g. FEBS Lett 1992;310:1721.
65. Pralong E, Vesin M-F, Droz B. Prostaglandin E2 receptors in the chicken spinal cord. 1. Biochemical characterization. Eur J Neurosci 1990;2:897903.
66. Pralong E, Vesin M-F, Droz B. Prostaglandin E2 receptors in the chicken spinal cord. 2. Autoradiographic localization. Eur J Neurosci 1990;2:904908.
67. Rump LC, Wilde K, Schollmeyer P. Prostaglandin E2 inhibits noradrenaline release and purinergic pressor responses to renal nerve stimulation at 1 Hz in isolated kidneys of young spontaneously hypertensive rats. J Hypertens 1990;8:897908.
68. Samuelsson B. Leukotrienes: mediators of immediate hypersensitivity reaction and inflammation. Science 1983;220:568575.
69. Sautebin L, Spagnuolo C, Galli C, Galli G. A mass fragmentographic procedure for the simultaneous determination of HETE and PGF2a in the central nervous system. Prostaglandins 1977;16:985988.
70. Schalling M, Neil A, Terenius L, Lindgren JA, Miamoto T, Hökfelt T, Samuelsson B. Leukotriene C4 binding sites in the rat central nervous system. Eur J Pharmacol 1986;122:251257.
71. Schweitzer P, Madamba S, Siggins GR. Arachidonic acid metabolites as mediators of somatostatin-induced increase in neuronal M-current. Nature 1990;346:464467.
72. Seregi A, Keller M, Hertting G. Are cerebral prostanoids of astroglial origin? Studies on the prostanoid forming system in developing rat brain and primary cultures of rat astrocytes. Brain Res 1987;404:113120.
73. Shearman MS, Naor Z, Sekiguchi K, Kishimoto A, Nishizuka Y. Selective activation of the g-subspecies of protein kinase C from bovine cerebellum by arachidonic acid and its lipoxygenase metabolites. FEBS Lett 1989;243:177182.
74. Shimizu T, Yamashita A, Hayaishi O. Specific binding of prostaglandin D2 to rat brain synaptic membrane. Occurrence, properties, and distribution. J Biol Chem 1982;257:1357013575.
75. Shimizu T, Takusagawa Y, Izumi T, Ohishi N, Seyama Y. Enzymic synthesis of leukotriene B4 in guinea pig brain. J Neurochem 1987;48:15411546.
76. Sugimoto Y, Namba T, Honda A, Hayashi Y, Negishi M, Ichikawa A, Narumiya S. Cloning and expression of a cDNA for mouse prostaglandin receptor EP3 subtype. J Biol Chem 1992;267:64636466.
77. Sun GY, MacQuarry RA. Deacylation-reacylation of arachidonoyl groups in cerebral phospholipids. In: Barkai AI, Bazan NG, ed. Arachidonic acid metabolism in the nervous system. Annals of the New York Academy of Sciences, vol 559. New York: New York Academy of Sciences, 1989;3755.
78. Traiffort E, Ruat M, Arrang J-M, Leurs R, Piomelli D, Schwartz J-C. Expression of a cloned rat histamine H2 receptor mediating inhibition of arachidonate release and activation of cAMP accumulation. Proc Natl Acad Sci USA 1992;89:26492653.
79. Urade Y, Fujimoto N, Hayaishi O. Purification and characterization of rat brain prostaglandin D synthetase. J Biol Chem 1985; 260:1241012415.
80. Urade Y, Fujimoto N, Kaneko T, Konishi A, Mizuno N, Hayaishi O. Postnatal changes in the localization of prostaglandin D synthetase from neurons to oligodendrocytes in the rat brain. J Biol Chem 1987;262:1513215136.
81. Vesin MF, Barakat-Walter I, Droz B. Preferential synthesis of prostaglandin D2 by neurons and prostaglandin E2 by fibroblasts and nonneuronal cells in chick dorsal root ganglia. J Neurochem 1991;57:167174.
82. Waite M. The phospholipases. In: Hanahan DJ, ed. Handbook of lipid research, vol. 5. New York: Plenum Press, 1987.
83. Waku K. Origins and fates of fatty acyl-CoA esters. Biochim Biophys Acta 1992;1124:101111.
84. Warner M, Köhler C, Hansson T, Gustafsson J-A. Regional distribution of cytochrome P-450 in the rat brain: spectral quantitation and contribution of P-450b,e and P-450c,d. J Neurochem 1988; 50:10571065.
85. Watanabe Y, Tokumoto H, Yamashita A, Narumiya S, Mizuno N, Hayaishi O. Specific bindings of prostaglandin D2, E2 and F2a in postmortem human brain. Brain Res 1985;342:110116.
86. Watanabe Y, Watanabe Y, Hamada K, Bommelaer-Bayt MC, Dray F, Kaneko T, Watanabe T, Medina JF, Haeggstrom JZ, Radmark O, Samuelsson B. Molecular cloning of a 12-lipoxygenase from rat brain. Eur J Biochem 1993;212:605612.
87. Williams JH, Errington ML, Lynch MA, Bliss TVP. Arachidonic acid induces a long-term activity-dependent enhancement of synaptic transmission in the hippocampus. Nature 1989;341:739742.
88. Wilson DB, Prescott SM, Majerus PW. Discovery of an arachidonoyl coenzyme A synthetase in human platelets. J Biol Chem 1982;257:35103515.
89. Wolfe LS, Pellerin L. Arachidonic acid metabolites in the rat and human brain. In: Barkai AI, Bazan NG, ed. Arachidonic acid metabolism in the nervous system. Annals of the New York Academy of Sciences, vol 559. New York: New York Academy of Sciences, 1989;7483.
90. Yamamoto S. Mammalian lipoxygenases: molecular structure and functions. Biochim Biophys Acta 1992;1128:117131.
91. Yamashita A, Watanabe Y, Hayaishi O. Autoradiographic localization of a binding protein(s) specific for prostaglandin D2 in rat brain. Proc Natl Acad Sci USA 1983;80:61146118.
92. Yoshihara Y, Watanabe Y. Translocation of phospholipase A2 from cytosol to membranes in rat brain induced by calcium ions. Biochem Biophys Res Commun 1990;170:484490.
93. Yu ACH, Chan PH, Fishman RA. Arachidonic acid inhibits uptake of glutamate and glutamine but not of GABA in cultured granule cells. J Neurosci Res 1987;424427.
published 2000